Cyclic hexapeptide somatostatin analogs
First Claim
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1. A compound having the formula:
- ##STR25## wherein R is ##STR26## such that the broken line indicates that the ring may be either cyclohexyl or phenyl;
m is 0 or 1; and
p is 0 when the ring is cyclohexyl and 1 when the ring is phenyl;
X is (CH2)n wherein n is 0, 1 or 2, sulfur;
R1 and R2 are independently lower alkyl, benzyl, substituted benzyl wherein the substitutent may be one or two of loweralkyl, halogen, hydroxy, amino, nitro or loweralkoxy; and
loweralkyl substituted with hydroxy, 3-indolylmethyl, carboxy, amino, guanidino, or a 5- or 6-membered heterocyclic ring;
R3 is 3-indolylmethyl or substituted 3-indolylmethyl wherein the substituent may be loweralkyl, loweralkoxy or halogen;
R4 is loweralkyl, hydroxyloweralkyl, benzyl, carboxyloweralkyl, aminoloweralkyl, 3-indolylmethyl or substituted hydroxy benzyl wherein the substituent may be loweralkyl, loweralkoxy, hydroxy, halogen, amino or nitro, or a 5- or 6-membered heterocyclic ring;
R5 is loweralkyl, benzyl, or substituted benzyl wherein the substituent is loweralkyl, loweralkoxy, hydroxy, halogen, amino or nitro; and
R6 and R7 are independently hydrogen or methyl.
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Abstract
Somatostatin analogs are prepared wherein a cyclic hexapeptide contains a secondary amino acid which replaces seven of the ring amino acids of somatostatin. The cyclic hexapeptides are easier to synthesize, have a longer duration of activity, and many have a greater level of activity than somatostatin. The compounds have the properties of inhibiting the release of glucagon, growth hormone and insulin. Certain of the compounds also are capable of inhibiting the release of gastric acid secretions. The compounds are particularly useful in the treatment of acromegaly, diabetes, diabetic retinopathy and peptic ulcers. These cyclic hexapeptides are prepared by the solid phase method.
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11 Claims
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1. A compound having the formula:
- ##STR25## wherein R is ##STR26## such that the broken line indicates that the ring may be either cyclohexyl or phenyl;
m is 0 or 1; and
p is 0 when the ring is cyclohexyl and 1 when the ring is phenyl;X is (CH2)n wherein n is 0, 1 or 2, sulfur; R1 and R2 are independently lower alkyl, benzyl, substituted benzyl wherein the substitutent may be one or two of loweralkyl, halogen, hydroxy, amino, nitro or loweralkoxy; and
loweralkyl substituted with hydroxy, 3-indolylmethyl, carboxy, amino, guanidino, or a 5- or 6-membered heterocyclic ring;R3 is 3-indolylmethyl or substituted 3-indolylmethyl wherein the substituent may be loweralkyl, loweralkoxy or halogen; R4 is loweralkyl, hydroxyloweralkyl, benzyl, carboxyloweralkyl, aminoloweralkyl, 3-indolylmethyl or substituted hydroxy benzyl wherein the substituent may be loweralkyl, loweralkoxy, hydroxy, halogen, amino or nitro, or a 5- or 6-membered heterocyclic ring; R5 is loweralkyl, benzyl, or substituted benzyl wherein the substituent is loweralkyl, loweralkoxy, hydroxy, halogen, amino or nitro; and R6 and R7 are independently hydrogen or methyl. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
- ##STR25## wherein R is ##STR26## such that the broken line indicates that the ring may be either cyclohexyl or phenyl;
Specification